One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature

doi:10.6023/cjoc201911010

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1331-1336.DOI: 10.6023/cjoc201911010 Previous Articles Next Articles

室温条件下“一锅多组分”脯氨酸催化合成N,O-缩醛化合物

兰金, 谢宗波, 杨江楠, 孟佳, 刘一帅, 乐长高

东华理工大学应用化学系南昌 330013

收稿日期:2019-11-06 修回日期:2019-12-19 发布日期:2020-01-21
通讯作者: 谢宗波, 乐长高 E-mail:zbxie@ecut.edu.cn;zhgle@ecit.cn
基金资助:
国家自然科学基金（Nos.21462001，11765002）、江西省科技计划（No.20161BCB24006）、江西省教育厅科技（Nos.KJLD14050，GJJ150584）资助项目.

One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature

Lan Jin, Xie Zongbo, Yang Jiangnan, Meng Jia, Liu Yishuai, Le Zhanggao

Department of Applied Chemistry, East China University of Technology, Nanchang 330013

Received:2019-11-06 Revised:2019-12-19 Published:2020-01-21
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21462001, 11765002), the Science and Technology Projects of Jiangxi Province (No. 20161BCB24006), and the Science and Technology Foundation of Jiangxi Provincial Department of Education (Nos. KJLD14050, GJJ150584).

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Lan Jin, Xie Zongbo, Yang Jiangnan, Meng Jia, Liu Yishuai, Le Zhanggao. One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1331-1336.

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[1] Li, G.; Fronczek, F. R.; Antilla, J. C. J. Am. Chem. Soc. 2008, 130, 12216.
[2] Tanaka, J. I.; Higa, T. Tetrahedron Lett. 1996, 37, 5535.
[3] Jiang, X.; Williams, N.; De Brabander, J. K. Org. Lett. 2007, 9, 227.
[4] Chen, G.; Patanapongpibul, M.; Jiang, Z.; Zhang, Q.; Zheng, S.; Wang, G.; White, J. D.; Chen, Q. H. Org. Biomol. Chem. 2019, 17, 3830.
[5] Mosey, R. A.; Floreancig, P. E. Nat. Prod. Rep. 2012, 29, 980.
[6] Li, M.; Luo, B.; Liu, Q.; Hu, Y.; Ganesan, A.; Huang, P.; Wen, S. Org. Lett. 2013, 16, 10.
[7] Huang, Y. Y.; Cai, C.; Yang, X. ACS Catal. 2016, 6, 5747.
[8] Downey, C. W.; Lee, A. Y. K.; Goodin, J. R.; Botelho, C. J.; Stith, W. M. Tetrahedron Lett. 2017, 58, 3496.
[9] Zhang, Q.; Xu, D.; Yang, J.; He, L.; Zhang, M. Tetrahedron Lett. 2019, 60, 150992.
[10] Fletcher, J. T.; Christensen, J. A.; Villa, E. M. Tetrahedron Lett. 2017, 58, 4450.
[11] Traboni, S.; Bedini, E.; Giordano, M.; Iadonisi, A. Tetrahedron Lett. 2019, 60, 1777.
[12] Lillo, V. J.; Mansilla, J.; Saá, J. M. Org. Biomol. Chem. 2018, 16, 4527.
[13] Wan S. Y.; Green, M. E.; Park, J. H.; Floreancig, P. E. Org. Lett. 2007, 9, 5385.
[14] Danson, K. J. Y.; Richard, J. A. Tetrahedron Lett. 2014, 55, 2183.
[15] Narina, S. V.; Sudalai, A. Tetrahedron Lett. 2006, 47, 6799.
[16] Basumatary, G.; Mohanta, R.; Bez, G. Catal. Lett. 2019, 149, 2776.
[17] Wu, H.; Liu, H.; Li, J.; Li, X.; Xiao, H. P.; Jiang, J. Synlett 2019, 30, 1241.
[18] Lucas, F. D. C.; Simone, C. S.; Matheus, V. M.; Paloma, S. P.; Alberto, W. J.; Diogo, M. V.; José Augusto, F. P. V. J. Braz. Chem. Soc. 2018, 30, 893.
[19] Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600.
[20] Bhattacharjee, D.; Sutradhar, D.; Chandra, A. K.; Myrboh, B. Tetrahedron 2017, 73, 3497.
[21] König, S.; Marco, H.; Gäde, G. Amino Acids 2017, 50, 359.
[22] Allen, W. D.; Czinki, E.; Csaszar, A. G. Chem.-Eur. J. 2004, 10, 4512.
[23] Usui, I.; Schmidt, S.; Breit, B. Org. Lett. 2009, 11, 1453.
[24] Morales, S.; Guijarro, F. G.; García Ruano, J. L.; Cid, M. B. J. Am. Chem. Soc. 2014, 136, 1082.

室温条件下“一锅多组分”脯氨酸催化合成N,O-缩醛化合物

One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature

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